Methyl phenylacetate → (1-Methoxy-2-phenylvinyloxy)trimethylsilane

HRID 440390Notes

Reaction equation

HRID 440390 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O([Si:20]([CH3:23])([CH3:22])[CH3:21])S(C(F)(F)F)(=O)=O.C(N(CC)CC)C>CCOCC.ClCCl>[CH3:11][O:10][C:8]([O:9][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7559Methyl phenylacetateHCID 8471TriethylamineHCID 65367Trimethylsilyl triflate

Product 1

HCID 54141957(1-Methoxy-2-phenylvinyloxy)trimethylsilane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Cool methyl phenylacetate (1.80 mL, 12.5 mmol) to 0° C. using and ice/water bath. Add dropwise and with vigorous stirring, a solution of trimethylsilyl triflate (2.70 mL, 4 mmol) and triethylamine (1.95 mL, 14 mmol) in dry ether (25 mL). When the addition is complete, warm slowly to ambient temperature. After 4.5 hours, cool in an ice/bath to obtain a heavier reddish oil. Remove the reddish oil by syringe. Evaporate the ether under high vacuum at 0° C. to obtain a residue and dissolve the residue in dichloromethane (25 mL) to give the title compound as a solution in dichloromethane which is used without further purification.

Workup

  1. additionAdd dropwise and with vigorous stirring
  2. additionWhen the addition
  3. temperaturecool in an ice/bath
  4. customto obtain a heavier reddish oil
  5. customRemove the reddish oil by syringe
  6. customEvaporate the ether under high vacuum at 0° C.
  7. customto obtain a residue

Sources & evidence

ORD record
ord-daf8c713236449fcbf1659b4e82a1c40
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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